JPS60234588A - 長鎖高度不飽和脂肪酸アルコ−ルエステルの製造法 - Google Patents
長鎖高度不飽和脂肪酸アルコ−ルエステルの製造法Info
- Publication number
- JPS60234588A JPS60234588A JP59090797A JP9079784A JPS60234588A JP S60234588 A JPS60234588 A JP S60234588A JP 59090797 A JP59090797 A JP 59090797A JP 9079784 A JP9079784 A JP 9079784A JP S60234588 A JPS60234588 A JP S60234588A
- Authority
- JP
- Japan
- Prior art keywords
- fatty acid
- long
- unsaturated fatty
- highly unsaturated
- chain highly
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- -1 unsaturated fatty acid alcohol ester Chemical class 0.000 title claims abstract description 18
- 235000021122 unsaturated fatty acids Nutrition 0.000 title claims abstract description 13
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 22
- 229930195729 fatty acid Natural products 0.000 claims abstract description 22
- 239000000194 fatty acid Substances 0.000 claims abstract description 22
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 20
- 239000004367 Lipase Substances 0.000 claims abstract description 17
- 102000004882 Lipase Human genes 0.000 claims abstract description 17
- 108090001060 Lipase Proteins 0.000 claims abstract description 17
- 235000019421 lipase Nutrition 0.000 claims abstract description 17
- 150000004670 unsaturated fatty acids Chemical class 0.000 claims abstract description 8
- 150000005846 sugar alcohols Polymers 0.000 claims abstract description 6
- 150000001298 alcohols Chemical class 0.000 claims description 4
- 150000004668 long chain fatty acids Chemical class 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 8
- 238000005886 esterification reaction Methods 0.000 abstract description 7
- 239000000203 mixture Substances 0.000 abstract description 7
- 230000032050 esterification Effects 0.000 abstract description 6
- 230000003301 hydrolyzing effect Effects 0.000 abstract description 4
- 241001465754 Metazoa Species 0.000 abstract description 2
- 244000005700 microbiome Species 0.000 abstract description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 17
- 239000003921 oil Substances 0.000 description 13
- 235000019198 oils Nutrition 0.000 description 13
- 238000000034 method Methods 0.000 description 12
- 108090000790 Enzymes Proteins 0.000 description 10
- 102000004190 Enzymes Human genes 0.000 description 10
- 239000003925 fat Substances 0.000 description 10
- 235000019197 fats Nutrition 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 8
- 238000006460 hydrolysis reaction Methods 0.000 description 8
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 description 8
- 238000005809 transesterification reaction Methods 0.000 description 8
- 241000222120 Candida <Saccharomycetales> Species 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 241000235527 Rhizopus Species 0.000 description 6
- MBMBGCFOFBJSGT-KUBAVDMBSA-N all-cis-docosa-4,7,10,13,16,19-hexaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O MBMBGCFOFBJSGT-KUBAVDMBSA-N 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 230000007062 hydrolysis Effects 0.000 description 5
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 239000012298 atmosphere Substances 0.000 description 4
- 239000004202 carbamide Substances 0.000 description 4
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 4
- 235000020669 docosahexaenoic acid Nutrition 0.000 description 4
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 4
- 235000021323 fish oil Nutrition 0.000 description 4
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 241000228212 Aspergillus Species 0.000 description 2
- 241000228245 Aspergillus niger Species 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 241000159512 Geotrichum Species 0.000 description 2
- BGNXCDMCOKJUMV-UHFFFAOYSA-N Tert-Butylhydroquinone Chemical compound CC(C)(C)C1=CC(O)=CC=C1O BGNXCDMCOKJUMV-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 229940090949 docosahexaenoic acid Drugs 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 235000020673 eicosapentaenoic acid Nutrition 0.000 description 2
- 238000001640 fractional crystallisation Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 230000002366 lipolytic effect Effects 0.000 description 2
- 238000000199 molecular distillation Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- TYWMIZZBOVGFOV-UHFFFAOYSA-N tetracosan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCO TYWMIZZBOVGFOV-UHFFFAOYSA-N 0.000 description 2
- 150000003626 triacylglycerols Chemical class 0.000 description 2
- 239000010698 whale oil Substances 0.000 description 2
- 239000004255 Butylated hydroxyanisole Substances 0.000 description 1
- 239000004322 Butylated hydroxytoluene Substances 0.000 description 1
- 229920001661 Chitosan Polymers 0.000 description 1
- 241000195649 Chlorella <Chlorellales> Species 0.000 description 1
- 108010093096 Immobilized Enzymes Proteins 0.000 description 1
- 241000235395 Mucor Species 0.000 description 1
- 241000228143 Penicillium Species 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- JAZBEHYOTPTENJ-JLNKQSITSA-N all-cis-5,8,11,14,17-icosapentaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O JAZBEHYOTPTENJ-JLNKQSITSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 description 1
- 239000003833 bile salt Substances 0.000 description 1
- 229940093761 bile salts Drugs 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 235000019282 butylated hydroxyanisole Nutrition 0.000 description 1
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229960005135 eicosapentaenoic acid Drugs 0.000 description 1
- JAZBEHYOTPTENJ-UHFFFAOYSA-N eicosapentaenoic acid Natural products CCC=CCC=CCC=CCC=CCC=CCCCC(O)=O JAZBEHYOTPTENJ-UHFFFAOYSA-N 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 235000021588 free fatty acids Nutrition 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 229940106134 krill oil Drugs 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 238000000622 liquid--liquid extraction Methods 0.000 description 1
- 238000003541 multi-stage reaction Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 210000000496 pancreas Anatomy 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000004250 tert-Butylhydroquinone Substances 0.000 description 1
- 235000019281 tert-butylhydroquinone Nutrition 0.000 description 1
- 235000010384 tocopherol Nutrition 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 235000021081 unsaturated fats Nutrition 0.000 description 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59090797A JPS60234588A (ja) | 1984-05-07 | 1984-05-07 | 長鎖高度不飽和脂肪酸アルコ−ルエステルの製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59090797A JPS60234588A (ja) | 1984-05-07 | 1984-05-07 | 長鎖高度不飽和脂肪酸アルコ−ルエステルの製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60234588A true JPS60234588A (ja) | 1985-11-21 |
| JPH0529433B2 JPH0529433B2 (enrdf_load_stackoverflow) | 1993-04-30 |
Family
ID=14008573
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59090797A Granted JPS60234588A (ja) | 1984-05-07 | 1984-05-07 | 長鎖高度不飽和脂肪酸アルコ−ルエステルの製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60234588A (enrdf_load_stackoverflow) |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61246146A (ja) * | 1985-04-23 | 1986-11-01 | Nitsusui Seiyaku Kk | エイコサペンタエノイルグリセライド含有脂質低下剤 |
| JPS6291188A (ja) * | 1985-10-17 | 1987-04-25 | Nisshin Oil Mills Ltd:The | 高度不飽和脂肪酸グリセリドの製造法 |
| JPS62153249A (ja) * | 1985-12-27 | 1987-07-08 | Nisshin Flour Milling Co Ltd | エイコサペンタエン酸のグリセリド、その製法及びそれを含有する油脂製品 |
| JPS62185049A (ja) * | 1986-02-07 | 1987-08-13 | Nisshin Flour Milling Co Ltd | ドコサヘキサエン酸のグリセリンエステル及びその製法 |
| JPS62226947A (ja) * | 1986-03-27 | 1987-10-05 | Nisshin Flour Milling Co Ltd | 高度不飽和高級脂肪酸のモノグリセリドおよびその製法 |
| JPH01291798A (ja) * | 1988-05-20 | 1989-11-24 | Soda Koryo Kk | 脂肪酸の製造法 |
| WO1996026287A1 (fr) * | 1995-02-24 | 1996-08-29 | Goemar S.A. | Procedes enzymatiques d'enrichissement en acides gras polyinsatures |
| US5945318A (en) * | 1994-03-08 | 1999-08-31 | Norsk Hydro A.S. | Refining oil compositions |
| JP2008526217A (ja) * | 2005-01-10 | 2008-07-24 | ノボザイムス アクティーゼルスカブ | ２つの脂肪分解酵素を使用する脂肪酸アルキルエステルの製造 |
| CN110878289A (zh) * | 2019-12-26 | 2020-03-13 | 中国海洋大学 | 一种脂肪酶及其应用 |
-
1984
- 1984-05-07 JP JP59090797A patent/JPS60234588A/ja active Granted
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61246146A (ja) * | 1985-04-23 | 1986-11-01 | Nitsusui Seiyaku Kk | エイコサペンタエノイルグリセライド含有脂質低下剤 |
| JPS6291188A (ja) * | 1985-10-17 | 1987-04-25 | Nisshin Oil Mills Ltd:The | 高度不飽和脂肪酸グリセリドの製造法 |
| JPS62153249A (ja) * | 1985-12-27 | 1987-07-08 | Nisshin Flour Milling Co Ltd | エイコサペンタエン酸のグリセリド、その製法及びそれを含有する油脂製品 |
| JPS62185049A (ja) * | 1986-02-07 | 1987-08-13 | Nisshin Flour Milling Co Ltd | ドコサヘキサエン酸のグリセリンエステル及びその製法 |
| JPS62226947A (ja) * | 1986-03-27 | 1987-10-05 | Nisshin Flour Milling Co Ltd | 高度不飽和高級脂肪酸のモノグリセリドおよびその製法 |
| JPH01291798A (ja) * | 1988-05-20 | 1989-11-24 | Soda Koryo Kk | 脂肪酸の製造法 |
| US5945318A (en) * | 1994-03-08 | 1999-08-31 | Norsk Hydro A.S. | Refining oil compositions |
| WO1996026287A1 (fr) * | 1995-02-24 | 1996-08-29 | Goemar S.A. | Procedes enzymatiques d'enrichissement en acides gras polyinsatures |
| JP2008526217A (ja) * | 2005-01-10 | 2008-07-24 | ノボザイムス アクティーゼルスカブ | ２つの脂肪分解酵素を使用する脂肪酸アルキルエステルの製造 |
| US9593352B2 (en) | 2005-01-10 | 2017-03-14 | Novozymes A/S | Production of fatty acid alkyl esters by use of two lipolytic enzymes |
| CN110878289A (zh) * | 2019-12-26 | 2020-03-13 | 中国海洋大学 | 一种脂肪酶及其应用 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0529433B2 (enrdf_load_stackoverflow) | 1993-04-30 |
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